Hilary Duff: Her Allure Photo Shoot

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Clean-cut reputation aside, Hilary Duff says she's no "perfect prude girl. I like to do normal things that 20-year-olds do." Well, any other 20-year-old with two movies on deck, a new album, and a multimillion-dollar empire, that is.

Inspired by the 1967 film Bonnie and Clyde, Allure creative director Paul Cavaco dressed Duff in a Marc by Marc Jacobs sweater, a dress by Derek Lam, a scarf by Chanel, and a beret by Kokin. Makeup artist Brigitte Reiss-Andersen modeled Duff's makeup after Faye Dunaway's in the movie, while Duff posed in a "sexy Midwestern way." Reiss-Andersen used a "ton of lashes," a dab of white-gold shadow in the inner corners, a blonde brow gel to mute her eyebrows, and a pink-peach blush. Reiss-Andersen created "barely there" lips with a dark beige pencil because "Hilary's a gorgeous girl. I wanted that to come through."

Duff is now taking on more adult roles: She plays an "oversexed" Eastern European pop star in War, Inc., and a girl obsessed with suicide in Greta. Is she worried this will alienate her Lizzie McGuire fans? "I don't want to restrict myself from doing things that stimulate me just to make them happy...if they continue liking me, that's cool, but I don't want to cater to them. I'm not 13, 14, or 15 anymore." Here, Duff poses for Thompson.

Although she says: "I'm not good at loving the red carpet and knowing how to pose the way you're supposed to," Duff has had boyfriends in common with Lindsay Lohan and Nicole Ritchie. At 15 she began dating Good Charlotte singer Joel Madden, then 24. With almost a decade between their ages, "He was never nervous, like, 'I could get arrested,'" she says. But she does admit, "It looked bad." These days she's with New York Islanders center Mike Comrie. Duff discusses the shoot with Allure creative director Paul Cavaco and hairstylist Serge Normant.

Growing up in the spotlight, Duff felt pressure to diet, but says she's eased up. Duff felt the scrutiny of her appearance: "I don't think I ever looked sick, but I really watched what I ate. You lose touch when you're so obsessed."

Duff was number seven on Forbes magazine's "Richest Celebrities and Stars under 25" and has a Barbie made in her likeness. "[Mattel] would send over boxes of Barbie heads that looked like me. It was so bizarre." Regardless, she's managed to avoid becoming another self-destructive young star. "I don't want that attention. If I can't get any from what I'm doing now, I'll figure out a different plan."